One-pot access to L-5,6-dihalotryptophans and L-alknyltryptophans using tryptophan synthase

被引：9

作者：

Corr, Michael J. ^{[1
]}

Smith, Duncan R. M. ^{[1
]}

Goss, Rebecca J. M. ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

来源：

TETRAHEDRON | 2016年 / 72卷 / 46期

基金：

欧洲研究理事会;

关键词：

Biotransformation; Dihalotryptophan; Alkynyltryptophan; Tryptophan synthase;

D O I：

10.1016/j.tet.2016.02.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report, for the first time, the use of tryptophan synthase in the generation of L-dihalotryptophans and L-alkynyltryptophans. These previously unpublished compounds will be useful tools in the generation of probes for chemical biology, in biosynthetic diversification and as convenient building blocks for synthesis. (C) 2016 Published by Elsevier Ltd.

引用

页码：7306 / 7310

页数：5

共 15 条

[1] ENZYMATIC AND CHEMICAL MODIFICATIONS OF LIPOPEPTIDE ANTIBIOTIC A21978C - THE SYNTHESIS AND EVALUATION OF DAPTOMYCIN (LY146032) [J].

DEBONO, M ;

ABBOTT, BJ ;

MOLLOY, RM ;

FUKUDA, DS ;

HUNT, AH ;

DAUPERT, VM ;

COUNTER, FT ;

OTT, JL ;

CARRELL, CB ;

HOWARD, LC ;

BOECK, LD ;

HAMILL, RL .

JOURNAL OF ANTIBIOTICS, 1988, 41 (08) :1093-1105

[2] Cation-pi interactions in chemistry and biology: A new view of benzene, Phe, Tyr, and Trp [J].

Dougherty, DA .

SCIENCE, 1996, 271 (5246) :163-168

[3] ABSOLUTE-CONFIGURATION OF STAUROSPORINE BY X-RAY-ANALYSIS [J].

FUNATO, N ;

TAKAYANAGI, H ;

KONDA, Y ;

TODA, Y ;

HARIGAYA, Y ;

IWAI, Y ;

OMURA, S .

TETRAHEDRON LETTERS, 1994, 35 (08) :1251-1254

[4]

Goss R. J. M., 2006, CHEM COMMUN, V4924

[5]

HOPWOOD DA, 1983, J GEN MICROBIOL, V129, P3575

[6] ISOLATION AND STRUCTURE DETERMINATION OF DIAZONAMIDE-A AND DIAZONAMIDE-B, UNUSUAL CYTOTOXIC METABOLITES FROM THE MARINE ASCIDIAN DIAZONA-CHINENSIS [J].

LINDQUIST, N ;

FENICAL, W ;

VANDUYNE, GD ;

CLARDY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2303-2304

[7] ROLE OF CHANCE OBSERVATIONS IN CHEMOTHERAPY - VINCA-ROSEA [J].

NOBLE, RL ;

BEER, CT ;

CUTTS, JH .

ANNALS OF THE NEW YORK ACADEMY OF SCIENCES, 1958, 76 (03) :882-894

[8] HYDROPHOBICITY OF AMINO-ACID RESIDUES IN GLOBULAR-PROTEINS [J].

ROSE, GD ;

GESELOWITZ, AR ;

LESSER, GJ ;

LEE, RH ;

ZEHFUS, MH .

SCIENCE, 1985, 229 (4716) :834-838

[9] Gene Expression Enabling Synthetic Diversification of Natural Products: Chemogenetic Generation of Pacidamycin Analogs [J].

Roy, Abhijeet Deb ;

Grueschow, Sabine ;

Cairns, Nickiwe ;

Goss, Rebecca J. M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (35) :12243-12245

[10]

Rydon H. N., 1955, J CHEM SOC, V3499

← 1 2 →